We investigate the singularities of the trace of the half-wave group, $mathrm{Tr} , e^{-itsqrtDelta}$, on Euclidean surfaces with conical singularities $(X,g)$. We compute the leading-order singularity associated to periodic orbits with successive degenerate diffractions. This result extends the previous work of the third author cite{Hil} and the two-dimensional case of the work of the first author and Wunsch cite{ForWun} as well as the seminal result of Duistermaat and Guillemin cite{DuiGui} in the smooth setting. As an intermediate step, we identify the wave propagators on $X$ as singular Fourier integral operators associated to intersecting Lagrangian submanifolds, originally developed by Melrose and Uhlmann cite{MelUhl}.